HRP20020174A2 - Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same - Google Patents
Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same Download PDFInfo
- Publication number
- HRP20020174A2 HRP20020174A2 HR20020174A HRP20020174A HRP20020174A2 HR P20020174 A2 HRP20020174 A2 HR P20020174A2 HR 20020174 A HR20020174 A HR 20020174A HR P20020174 A HRP20020174 A HR P20020174A HR P20020174 A2 HRP20020174 A2 HR P20020174A2
- Authority
- HR
- Croatia
- Prior art keywords
- methoxy
- compounds
- benzimidazole
- methyl
- sulfinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 175
- 125000003545 alkoxy group Chemical group 0.000 title claims description 67
- 239000000825 pharmaceutical preparation Chemical class 0.000 title claims description 55
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 499
- 239000000203 mixture Substances 0.000 claims description 369
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims description 171
- 150000003839 salts Chemical class 0.000 claims description 140
- 238000002360 preparation method Methods 0.000 claims description 137
- 239000004480 active ingredient Substances 0.000 claims description 105
- 239000012453 solvate Substances 0.000 claims description 73
- 150000004677 hydrates Chemical class 0.000 claims description 70
- 229920000858 Cyclodextrin Polymers 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 230000014509 gene expression Effects 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 241000124008 Mammalia Species 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 239000002775 capsule Substances 0.000 claims description 23
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 150000001768 cations Chemical group 0.000 claims description 20
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
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- 239000003085 diluting agent Substances 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 239000004615 ingredient Substances 0.000 claims description 14
- 210000004211 gastric acid Anatomy 0.000 claims description 13
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
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- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 6
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- -1 benzimidazole compound Chemical class 0.000 description 82
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- 239000000463 material Substances 0.000 description 36
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 34
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- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Chemical class 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000029219 regulation of pH Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- UGJCNRLBGKEGEH-UHFFFAOYSA-N sodium-binding benzofuran isophthalate Chemical compound COC1=CC=2C=C(C=3C(=CC(=CC=3)C(O)=O)C(O)=O)OC=2C=C1N(CCOCC1)CCOCCOCCN1C(C(=CC=1C=2)OC)=CC=1OC=2C1=CC=C(C(O)=O)C=C1C(O)=O UGJCNRLBGKEGEH-UHFFFAOYSA-N 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15087899P | 1999-08-26 | 1999-08-26 | |
US09/519,976 US6262085B1 (en) | 1999-08-26 | 2000-03-07 | Alkoxy substituted Benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
PCT/US2000/023363 WO2001014367A1 (en) | 1999-08-26 | 2000-08-25 | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20020174A2 true HRP20020174A2 (en) | 2005-12-31 |
Family
ID=26848119
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20020174A HRP20020174A2 (en) | 1999-08-26 | 2002-02-27 | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
Country Status (16)
Country | Link |
---|---|
EP (1) | EP1206466B1 (ru) |
JP (1) | JP4312405B2 (ru) |
KR (1) | KR100712039B1 (ru) |
CN (2) | CN1636564A (ru) |
AT (1) | ATE306483T1 (ru) |
AU (2) | AU777667B2 (ru) |
BR (1) | BR0014145A (ru) |
CA (1) | CA2382867A1 (ru) |
DE (1) | DE60023154T2 (ru) |
HR (1) | HRP20020174A2 (ru) |
MX (1) | MXPA02002007A (ru) |
NO (1) | NO326849B1 (ru) |
RO (1) | RO122491B1 (ru) |
RU (1) | RU2263673C2 (ru) |
SI (1) | SI20974A (ru) |
SK (1) | SK286903B6 (ru) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2376231A (en) * | 2001-06-06 | 2002-12-11 | Cipla Ltd | Benzimidazole-cyclodextrin inclusion complex |
EP1765806A1 (en) | 2004-06-24 | 2007-03-28 | AstraZeneca AB | New process for the preparation of crystal modifications for use in the preparation of esomeprazole sodium salt |
ES2246149B1 (es) * | 2004-07-02 | 2007-06-01 | Esteve Quimica, S.A. | Formas solidas de la sal magnesica de s-omeprazol y procedimientos para su preparacion. |
CN103524491A (zh) * | 2013-10-16 | 2014-01-22 | 江南大学 | 埃索美拉唑镁盐四水合物的三种晶型及其制备方法 |
CN114558004B (zh) * | 2022-03-29 | 2023-08-11 | 奎马特里克斯有限公司 | Qtx125药物制剂 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
SE8300736D0 (sv) * | 1983-02-11 | 1983-02-11 | Haessle Ab | Novel pharmacologically active compounds |
-
2000
- 2000-08-25 AU AU70737/00A patent/AU777667B2/en not_active Ceased
- 2000-08-25 EP EP00959404A patent/EP1206466B1/en not_active Expired - Lifetime
- 2000-08-25 CA CA002382867A patent/CA2382867A1/en not_active Abandoned
- 2000-08-25 CN CNA2004100946486A patent/CN1636564A/zh active Pending
- 2000-08-25 SK SK281-2002A patent/SK286903B6/sk not_active IP Right Cessation
- 2000-08-25 AT AT00959404T patent/ATE306483T1/de not_active IP Right Cessation
- 2000-08-25 RO ROA200200206A patent/RO122491B1/ro unknown
- 2000-08-25 CN CNB008149232A patent/CN1183127C/zh not_active Expired - Fee Related
- 2000-08-25 DE DE60023154T patent/DE60023154T2/de not_active Expired - Lifetime
- 2000-08-25 RU RU2002107421/04A patent/RU2263673C2/ru not_active IP Right Cessation
- 2000-08-25 BR BR0014145-3A patent/BR0014145A/pt not_active Application Discontinuation
- 2000-08-25 KR KR1020027002436A patent/KR100712039B1/ko not_active IP Right Cessation
- 2000-08-25 SI SI200020039A patent/SI20974A/sl not_active IP Right Cessation
- 2000-08-25 JP JP2001518698A patent/JP4312405B2/ja not_active Expired - Fee Related
- 2000-08-25 MX MXPA02002007A patent/MXPA02002007A/es active IP Right Grant
-
2002
- 2002-02-25 NO NO20020914A patent/NO326849B1/no not_active IP Right Cessation
- 2002-02-27 HR HR20020174A patent/HRP20020174A2/hr not_active Application Discontinuation
-
2005
- 2005-01-17 AU AU2005200203A patent/AU2005200203B2/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
NO20020914L (no) | 2002-04-26 |
KR20020035861A (ko) | 2002-05-15 |
RO122491B1 (ro) | 2009-07-30 |
AU2005200203B2 (en) | 2008-01-10 |
RU2263673C2 (ru) | 2005-11-10 |
CN1183127C (zh) | 2005-01-05 |
DE60023154T2 (de) | 2006-06-22 |
AU777667B2 (en) | 2004-10-28 |
ATE306483T1 (de) | 2005-10-15 |
SK286903B6 (sk) | 2009-07-06 |
SK2812002A3 (en) | 2002-07-02 |
DE60023154D1 (de) | 2006-02-23 |
CN1384831A (zh) | 2002-12-11 |
SI20974A (sl) | 2003-02-28 |
NO326849B1 (no) | 2009-03-02 |
CA2382867A1 (en) | 2001-03-01 |
NO20020914D0 (no) | 2002-02-25 |
BR0014145A (pt) | 2002-05-14 |
AU7073700A (en) | 2001-03-19 |
CN1636564A (zh) | 2005-07-13 |
MXPA02002007A (es) | 2003-08-20 |
AU2005200203A1 (en) | 2005-02-10 |
KR100712039B1 (ko) | 2007-04-27 |
EP1206466B1 (en) | 2005-10-12 |
JP4312405B2 (ja) | 2009-08-12 |
JP2003507475A (ja) | 2003-02-25 |
EP1206466A1 (en) | 2002-05-22 |
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